#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:54:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179546 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/15/4501591.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4501591
loop_
_publ_author_name
'Ma, Lu-Fang'
'Li, Cheng-Peng'
'Wang, Li-Ya'
'Du, Miao'
_publ_section_title
;
 Zn(II) and Cd(II) Coordination Polymers Assembled from a Versatile Tecton
 5-Nitro-1,2,3-benzenetricarboxylic Acid andN,N′-Donor Ancillary
 Coligands
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2641
_journal_paper_doi               10.1021/cg100139p
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C19 H13 N3 O9 Zn'
_chemical_formula_weight         492.69
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.5410(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.386(2)
_cell_length_b                   9.7824(9)
_cell_length_c                   14.8774(14)
_cell_measurement_reflns_used    4764
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.87
_cell_measurement_theta_min      2.54
_cell_volume                     3762.5(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11540
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_T_max  0.7427
_exptl_absorpt_correction_T_min  0.5867
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.597
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0422P)²+3.5255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0748
_reflns_number_gt                3044
_reflns_number_total             3488
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg100139p_si_002.cif
_cod_data_source_block           b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4501591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.874315(9) 0.14637(2) 0.299235(16) 0.02948(10) Uani 1 1 d .
O1 O 0.90714(6) 0.34407(18) 0.44283(12) 0.0466(4) Uani 1 1 d .
O2 O 0.83425(6) 0.23968(16) 0.37901(10) 0.0368(4) Uani 1 1 d .
O3 O 0.93587(7) 0.45923(18) 0.62918(12) 0.0480(4) Uani 1 1 d .
H3 H 0.9670 0.4753 0.6374 0.072 Uiso 1 1 d R
O4 O 0.92998(7) 0.6307(2) 0.52820(13) 0.0533(5) Uani 1 1 d .
O5 O 0.66366(6) 0.5677(2) 0.51459(12) 0.0509(5) Uani 1 1 d .
O6 O 0.66995(6) 0.39093(19) 0.42976(11) 0.0450(4) Uani 1 1 d .
O7 O 0.88696(7) 0.69720(17) 0.70792(11) 0.0441(4) Uani 1 1 d .
O8 O 0.81391(7) 0.80924(16) 0.67082(11) 0.0440(4) Uani 1 1 d .
N1 N 0.68888(7) 0.4841(2) 0.48109(12) 0.0350(4) Uani 1 1 d .
N2 N 0.85196(7) -0.05594(18) 0.28799(11) 0.0305(4) Uani 1 1 d .
N3 N 0.94486(7) 0.05480(18) 0.34403(12) 0.0327(4) Uani 1 1 d .
C1 C 0.82898(8) 0.4190(2) 0.48380(13) 0.0263(4) Uani 1 1 d .
C2 C 0.85263(8) 0.5186(2) 0.54660(13) 0.0275(4) Uani 1 1 d .
C3 C 0.82144(8) 0.6067(2) 0.58643(14) 0.0287(4) Uani 1 1 d .
C4 C 0.76787(8) 0.5973(2) 0.56268(14) 0.0301(5) Uani 1 1 d .
H4 H 0.7472 0.6591 0.5863 0.036 Uiso 1 1 calc R
C5 C 0.74577(8) 0.4956(2) 0.50385(14) 0.0279(4) Uani 1 1 d .
C6 C 0.77546(8) 0.4056(2) 0.46434(13) 0.0276(4) Uani 1 1 d .
H6 H 0.7598 0.3370 0.4252 0.033 Uiso 1 1 calc R
C7 C 0.86005(9) 0.3283(2) 0.43268(14) 0.0299(5) Uani 1 1 d .
C8 C 0.91086(9) 0.5425(2) 0.56564(15) 0.0372(5) Uani 1 1 d .
C9 C 0.84243(9) 0.7125(2) 0.65830(14) 0.0331(5) Uani 1 1 d .
C10 C 0.99072(10) 0.1166(3) 0.36965(18) 0.0437(6) Uani 1 1 d .
H10 H 0.9920 0.2116 0.3680 0.052 Uiso 1 1 calc R
C11 C 1.03609(10) 0.0454(3) 0.39830(18) 0.0487(6) Uani 1 1 d .
H11 H 1.0674 0.0910 0.4155 0.058 Uiso 1 1 calc R
C12 C 1.03384(10) -0.0952(3) 0.4009(2) 0.0525(7) Uani 1 1 d .
H12 H 1.0639 -0.1460 0.4197 0.063 Uiso 1 1 calc R
C13 C 0.98709(10) -0.1594(3) 0.3756(2) 0.0485(6) Uani 1 1 d .
H13 H 0.9852 -0.2543 0.3780 0.058 Uiso 1 1 calc R
C14 C 0.94268(8) -0.0835(2) 0.34640(14) 0.0325(5) Uani 1 1 d .
C15 C 0.89084(9) -0.1443(2) 0.31554(15) 0.0335(5) Uani 1 1 d .
C16 C 0.88131(11) -0.2841(3) 0.3144(2) 0.0542(7) Uani 1 1 d .
H16 H 0.9082 -0.3452 0.3345 0.065 Uiso 1 1 calc R
C17 C 0.83180(12) -0.3315(3) 0.2832(2) 0.0546(7) Uani 1 1 d .
H17 H 0.8251 -0.4249 0.2812 0.066 Uiso 1 1 calc R
C18 C 0.79239(10) -0.2403(3) 0.25524(16) 0.0443(6) Uani 1 1 d .
H18 H 0.7586 -0.2703 0.2345 0.053 Uiso 1 1 calc R
C19 C 0.80418(9) -0.1033(3) 0.25859(15) 0.0388(5) Uani 1 1 d .
H19 H 0.7776 -0.0409 0.2395 0.047 Uiso 1 1 calc R
O9 O 1.03417(7) 0.5316(2) 0.66714(17) 0.0491(5) Uani 1 1 d .
H1W H 1.0486(16) 0.550(4) 0.717(3) 0.100(16) Uiso 1 1 d .
H2W H 1.0492(16) 0.559(4) 0.630(3) 0.092(14) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 Zn1 N3 124.68(7) . .
O2 Zn1 N2 108.36(7) . .
N3 Zn1 N2 80.43(7) . .
O2 Zn1 O7 102.99(7) . 6_565
N3 Zn1 O7 105.94(7) . 6_565
N2 Zn1 O7 136.14(7) . 6_565
O2 Zn1 O8 92.71(6) . 6_565
N3 Zn1 O8 142.60(7) . 6_565
N2 Zn1 O8 88.51(6) . 6_565
O7 Zn1 O8 59.74(6) 6_565 6_565
O2 Zn1 C9 96.78(7) . 6_565
N3 Zn1 C9 129.91(7) . 6_565
N2 Zn1 C9 114.67(7) . 6_565
O7 Zn1 C9 30.23(7) 6_565 6_565
O8 Zn1 C9 29.67(7) 6_565 6_565
C7 O2 Zn1 114.11(14) . .
C8 O3 H3 109.3 . .
C9 O7 Zn1 92.40(13) . 6_566
C9 O8 Zn1 85.86(14) . 6_566
O5 N1 O6 124.25(19) . .
O5 N1 C5 117.88(19) . .
O6 N1 C5 117.87(18) . .
C19 N2 C15 119.5(2) . .
C19 N2 Zn1 126.65(15) . .
C15 N2 Zn1 113.88(15) . .
C10 N3 C14 118.98(19) . .
C10 N3 Zn1 127.21(16) . .
C14 N3 Zn1 113.81(14) . .
C6 C1 C2 120.08(18) . .
C6 C1 C7 118.05(18) . .
C2 C1 C7 121.82(19) . .
C3 C2 C1 119.11(19) . .
C3 C2 C8 118.82(18) . .
C1 C2 C8 121.80(18) . .
C4 C3 C2 120.32(19) . .
C4 C3 C9 115.81(18) . .
C2 C3 C9 123.8(2) . .
C5 C4 C3 119.34(19) . .
C5 C4 H4 120.3 . .
C3 C4 H4 120.3 . .
C4 C5 C6 121.7(2) . .
C4 C5 N1 118.93(18) . .
C6 C5 N1 119.34(18) . .
C5 C6 C1 119.27(19) . .
C5 C6 H6 120.4 . .
C1 C6 H6 120.4 . .
O1 C7 O2 124.03(19) . .
O1 C7 C1 120.03(19) . .
O2 C7 C1 115.93(19) . .
O4 C8 O3 125.7(2) . .
O4 C8 C2 122.0(2) . .
O3 C8 C2 112.3(2) . .
O8 C9 O7 121.4(2) . .
O8 C9 C3 118.6(2) . .
O7 C9 C3 119.9(2) . .
O8 C9 Zn1 64.47(12) . 6_566
O7 C9 Zn1 57.38(11) . 6_566
C3 C9 Zn1 168.95(15) . 6_566
N3 C10 C11 122.7(2) . .
N3 C10 H10 118.7 . .
C11 C10 H10 118.7 . .
C10 C11 C12 118.3(2) . .
C10 C11 H11 120.8 . .
C12 C11 H11 120.8 . .
C13 C12 C11 119.5(2) . .
C13 C12 H12 120.2 . .
C11 C12 H12 120.2 . .
C12 C13 C14 120.0(2) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
N3 C14 C13 120.5(2) . .
N3 C14 C15 115.82(18) . .
C13 C14 C15 123.7(2) . .
N2 C15 C16 120.3(2) . .
N2 C15 C14 116.04(19) . .
C16 C15 C14 123.6(2) . .
C17 C16 C15 119.5(2) . .
C17 C16 H16 120.2 . .
C15 C16 H16 120.2 . .
C18 C17 C16 119.7(3) . .
C18 C17 H17 120.2 . .
C16 C17 H17 120.2 . .
C17 C18 C19 118.1(2) . .
C17 C18 H18 120.9 . .
C19 C18 H18 120.9 . .
N2 C19 C18 122.9(2) . .
N2 C19 H19 118.5 . .
C18 C19 H19 118.5 . .
H1W O9 H2W 112(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O2 1.9651(14) .
Zn1 N3 2.0531(18) .
Zn1 N2 2.0623(18) .
Zn1 O7 2.1166(16) 6_565
Zn1 O8 2.2717(17) 6_565
Zn1 C9 2.511(2) 6_565
O1 C7 1.231(3) .
O2 C7 1.279(3) .
O3 C8 1.320(3) .
O3 H3 0.8200 .
O4 C8 1.192(3) .
O5 N1 1.222(2) .
O6 N1 1.229(2) .
O7 C9 1.265(3) .
O7 Zn1 2.1166(16) 6_566
O8 C9 1.246(3) .
O8 Zn1 2.2717(17) 6_566
N1 C5 1.475(3) .
N2 C19 1.332(3) .
N2 C15 1.342(3) .
N3 C10 1.338(3) .
N3 C14 1.354(3) .
C1 C6 1.390(3) .
C1 C2 1.406(3) .
C1 C7 1.512(3) .
C2 C3 1.402(3) .
C2 C8 1.524(3) .
C3 C4 1.390(3) .
C3 C9 1.511(3) .
C4 C5 1.375(3) .
C4 H4 0.9300 .
C5 C6 1.385(3) .
C6 H6 0.9300 .
C9 Zn1 2.511(2) 6_566
C10 C11 1.377(3) .
C10 H10 0.9300 .
C11 C12 1.377(4) .
C11 H11 0.9300 .
C12 C13 1.368(4) .
C12 H12 0.9300 .
C13 C14 1.382(3) .
C13 H13 0.9300 .
C14 C15 1.478(3) .
C15 C16 1.390(3) .
C16 C17 1.376(4) .
C16 H16 0.9300 .
C17 C18 1.370(4) .
C17 H17 0.9300 .
C18 C19 1.375(4) .
C18 H18 0.9300 .
C19 H19 0.9300 .
O9 H1W 0.78(4) .
O9 H2W 0.79(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H2W O1 0.79(4) 1.97(4) 2.751(3) 168(4) 5_766
O9 H1W O3 0.78(4) 2.41(4) 3.058(3) 141(4) 2_756
O9 H1W O7 0.78(4) 2.34(4) 2.977(3) 140(4) 2_756
O3 H3 O9 0.82 1.82 2.638(3) 171.3 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N3 Zn1 O2 C7 50.82(17) . .
N2 Zn1 O2 C7 141.78(14) . .
O7 Zn1 O2 C7 -69.34(15) 6_565 .
O8 Zn1 O2 C7 -128.89(15) 6_565 .
C9 Zn1 O2 C7 -99.39(15) 6_565 .
O2 Zn1 N2 C19 56.85(18) . .
N3 Zn1 N2 C19 -179.64(18) . .
O7 Zn1 N2 C19 -76.6(2) 6_565 .
O8 Zn1 N2 C19 -35.52(17) 6_565 .
C9 Zn1 N2 C19 -49.97(19) 6_565 .
O2 Zn1 N2 C15 -121.88(14) . .
N3 Zn1 N2 C15 1.63(15) . .
O7 Zn1 N2 C15 104.72(16) 6_565 .
O8 Zn1 N2 C15 145.76(15) 6_565 .
C9 Zn1 N2 C15 131.31(14) 6_565 .
O2 Zn1 N3 C10 -75.8(2) . .
N2 Zn1 N3 C10 178.5(2) . .
O7 Zn1 N3 C10 43.0(2) 6_565 .
O8 Zn1 N3 C10 103.8(2) 6_565 .
C9 Zn1 N3 C10 64.2(2) 6_565 .
O2 Zn1 N3 C14 104.45(15) . .
N2 Zn1 N3 C14 -1.33(15) . .
O7 Zn1 N3 C14 -136.74(15) 6_565 .
O8 Zn1 N3 C14 -76.03(18) 6_565 .
C9 Zn1 N3 C14 -115.57(15) 6_565 .
C6 C1 C2 C3 -2.3(3) . .
C7 C1 C2 C3 175.05(18) . .
C6 C1 C2 C8 -176.28(19) . .
C7 C1 C2 C8 1.1(3) . .
C1 C2 C3 C4 -1.2(3) . .
C8 C2 C3 C4 172.9(2) . .
C1 C2 C3 C9 176.71(18) . .
C8 C2 C3 C9 -9.1(3) . .
C2 C3 C4 C5 3.8(3) . .
C9 C3 C4 C5 -174.33(19) . .
C3 C4 C5 C6 -2.8(3) . .
C3 C4 C5 N1 178.32(18) . .
O5 N1 C5 C4 1.2(3) . .
O6 N1 C5 C4 -178.64(19) . .
O5 N1 C5 C6 -177.63(19) . .
O6 N1 C5 C6 2.5(3) . .
C4 C5 C6 C1 -0.7(3) . .
N1 C5 C6 C1 178.16(18) . .
C2 C1 C6 C5 3.2(3) . .
C7 C1 C6 C5 -174.19(18) . .
Zn1 O2 C7 O1 -8.4(3) . .
Zn1 O2 C7 C1 170.19(13) . .
C6 C1 C7 O1 174.6(2) . .
C2 C1 C7 O1 -2.8(3) . .
C6 C1 C7 O2 -4.1(3) . .
C2 C1 C7 O2 178.47(18) . .
C3 C2 C8 O4 -77.3(3) . .
C1 C2 C8 O4 96.7(3) . .
C3 C2 C8 O3 100.3(2) . .
C1 C2 C8 O3 -85.6(2) . .
Zn1 O8 C9 O7 -7.7(2) 6_566 .
Zn1 O8 C9 C3 168.08(17) 6_566 .
Zn1 O7 C9 O8 8.2(2) 6_566 .
Zn1 O7 C9 C3 -167.47(17) 6_566 .
C4 C3 C9 O8 -21.7(3) . .
C2 C3 C9 O8 160.3(2) . .
C4 C3 C9 O7 154.1(2) . .
C2 C3 C9 O7 -23.9(3) . .
C4 C3 C9 Zn1 81.8(9) . 6_566
C2 C3 C9 Zn1 -96.3(9) . 6_566
C14 N3 C10 C11 0.1(4) . .
Zn1 N3 C10 C11 -179.63(19) . .
N3 C10 C11 C12 -0.3(4) . .
C10 C11 C12 C13 -0.3(4) . .
C11 C12 C13 C14 1.0(4) . .
C10 N3 C14 C13 0.5(3) . .
Zn1 N3 C14 C13 -179.65(18) . .
C10 N3 C14 C15 -179.0(2) . .
Zn1 N3 C14 C15 0.9(2) . .
C12 C13 C14 N3 -1.1(4) . .
C12 C13 C14 C15 178.3(2) . .
C19 N2 C15 C16 -0.7(3) . .
Zn1 N2 C15 C16 178.13(19) . .
C19 N2 C15 C14 179.51(18) . .
Zn1 N2 C15 C14 -1.7(2) . .
N3 C14 C15 N2 0.6(3) . .
C13 C14 C15 N2 -178.9(2) . .
N3 C14 C15 C16 -179.2(2) . .
C13 C14 C15 C16 1.3(4) . .
N2 C15 C16 C17 1.1(4) . .
C14 C15 C16 C17 -179.1(2) . .
C15 C16 C17 C18 -1.1(4) . .
C16 C17 C18 C19 0.6(4) . .
C15 N2 C19 C18 0.2(3) . .
Zn1 N2 C19 C18 -178.43(17) . .
C17 C18 C19 N2 -0.2(4) . .
